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I started cycling yesterday! A couple of questions… I tried googling them as it’s really hard for a blind guy to search for things on Frank talk it south… I hate asking questions that have already been asked and I’m really sorry for doing this to you guys as I’m sure they have been answered or asked already…
How many pumps were you able to get in at first?
I’m getting four pumps in then the bulb goes golf ball on me… Should I push past this? Don’t really know if I can…
This guy is much much shorter and pointing up at 1 o’clock… When will it soften up and maybe bend a little bit? I’m asking for stretching sake and for the sake of comfortable sex thanks again, comrades!

No first hand experience. But consider these suggestions. Not everyone has the same implants so the volumes differ. There isn't a way to tell if two guys with the same size implant start pumping from the same filled level.
Way too many variables to consider. I would suggest that you are you. Pump until your body tells you no more. Whether from discomfort or the pump gets too hard. Btw, I think you're doing pretty good.

Solid advice, sir! Thanks for waking me up there…

I had the same issue at first. As you learn to use the pump, this should get better. Your tissue will stretch more. Also, make sure you have emptied the cylinders completely. I find that sometimes I have to do a couple of pumps, press the button again, and let it empty before I can pump correctly. You should feel a pop on the first pump if emptied correctly.